Asymmetric synthesis of tert -butyl ((1 R ,4a R ,8 R ,8a R )-1-hydroxyoctahydro-1 H -isochromen-8-yl)carbamate

Abstract The asymmetric synthesis of methyl ( E )-4-((1 R ,2 S ,3 R )-3-amino-2-(( E )-2-methoxycarbonyl-eten-1-yl)cyclohexyl)but-2-enoate 14 has been achieved from dimethyl (2 E ,7 E )-nona-2,7-dienedioate 2 . A key step is the asymmetric synthesis of 1-hydroxyoctahydro-1 H -isochromene derivative 5 whose X-ray analysis corroborated the stereochemistry of the new stereocenters. The asymmetric synthesis of the isochromenyl acetate derivative 11 shows the potential of this methodology for fused cyclohexanic system heterocyclic synthesis.